Frank Sinatra had it all. Then lost it all. Then got it all back tenfold. He was a man of extreme talent, confidence and insecurity. And he had powerful and dangerous friends. He orchestrated some of the greatest music ever made. And he also orchestrated an alliance between two friends—mob boss Sam Giancana and John F. Kennedy—that would help the latter win the White House and, in the end, prove disastrous for Frank and the country.